Natural sesquiterpenoids

Fraga, Braulio M.

doi:10.1039/b501837b

Cited by 90 publications

(45 citation statements)

References 339 publications

(271 reference statements)

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“…Sesquiterpenes possess a wide spectrum of biological activity through which they appear to play a role in plant defense mechanisms (Fraga 2001(Fraga , 2003. Due to their bioactivity, some sesquiterpenes with the cadinane skeleton have been evaluated for antifungal or insecticidal activity.…”

Section: Introductionmentioning

confidence: 99%

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Chien

Wang

et al. 2005

Holzforschung

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Cadinane-type sesquiterpenes have a wide spectrum of biological activity, but their use as wood preservatives and the structure-activity relationships of their derivatives have not yet been reported. A total of 13 compounds were synthesized from T-cadinol, T-muurolol, and a-cadinol and their chemical structures were confirmed by IR, MS, and 1 H and 13 C NMR. The antifungal properties of 16 compounds against three wood-decay fungi were evaluated in vitro. a-Cadinol showed strong antifungal activity against Lenzites betulina, Trametes versicolor, and Laetiporus sulphureus (total mean IC 50 0.10 mM). Among the derivatives synthesized, 3b-ethoxy-T-muurolol (0.24 mM), 4jH-cadinan-10b-ol (0.25 mM), 4jH-muurolan-10b-ol (0.29 mM), and 4jH-cadinan-10a-ol (0.25 mM) showed good antifungal activity against all fungi tested. Correlation was observed between the antifungal activity of the compounds tested and log P. Furthermore, the presence of an unsaturated double bond and oxygen-containing functional groups in the compounds plays a key role in their antifungal activity. The stereo configuration of cadinane-type sesquiterpenes also influences their antifungal activity. Understanding how the structure of natural compounds relates to their antifungal function is important and may facilitate their application as novel wood preservatives.

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Section: Introductionmentioning

confidence: 99%

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Chien

Wang

et al. 2005

Holzforschung

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“…representative components found in various vegetative species [5], have been demonstrated to be the major and potential precursors for SOAs formation [9,15,32].…”

Section: Introductionmentioning

confidence: 99%

UV-spectroscopy, electronic structure and ozonolytic reactivity of sesquiterpenes: a theoretical study

Zeng

2011

J Mol Model

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Sesquiterpenes, one of the most important classes of biogenic volatile organic compounds, are potentially significant precursors to secondary organic aerosols (SOAs) in nature. The electronic structure of sesquiterpenes and their reactivity in the ozonolysis reaction were investigated by density functional theory. Results from the CIS calculations combined with an analysis of transition intensities show that the first peaks in the ultraviolet (UV) spectra for saturated and unsaturated isomers are σ-σ* and π-π* transitions, respectively. The UV absorption wavelength and absorbency are dictated by the electronic structures of these compounds. An increase in the number of double bonds and formation of a conjugated system expand the range of absorption in the UV region. An isomer with an endocyclic C = C bond presents weaker UV transition intensity than its corresponding exocyclic isomer. Results from conceptual DFT chemical reactivity indices of isomers suggest that no quantitative linear relationships between the structural changes and their reactivity, such as different degrees of unsaturated C = C double bonds, or the number of substituents attached to the C = C bond were discovered. In the ozonolysis reaction of sesquiterpenes, isomers with larger steric hindrance of substituents or endocyclic C = C bond possess higher chemical reactivity compared to isomers with smaller steric hindrandce or with an exocyclic C = C bond. These results are imperative to a better understanding of SOAs production mechanisms in the troposphere.

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“…The bisabolane skeleton develops from the cyclization of the geranyl cation and results in the formation of a monocyclic ring structure [59]. In 2007, L. microcladia (Chios Is., North Aegean Sea) afforded the hydroxyl derivative of β -bisabolene, (66) [60], while, (5S)-5-acetoxy-β -bisabolene (67), was isolated, recently, from L. okamurai Yamada [61].…”

Section: Bisabolane Skeleton Sesquiterpenesmentioning

confidence: 99%

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

Al-Massarani¹

2014

Nat Prod Chem Res 2014

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Natural sesquiterpenoids

Abstract: This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. 421 references are cited.

Cited by 90 publications

References 339 publications

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

UV-spectroscopy, electronic structure and ozonolytic reactivity of sesquiterpenes: a theoretical study

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

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